This invention relates partially to new 1-(2-hydroxyaryl)-alkane-1-on-oximes, processes for their preparation, and their applicability to pharmaceutical preparations. The compounds in their own right and, consequently, the pharmaceutical products in which they are contained are characterised by useful pharmacological, especially anti-asthmatic, anti-anaphylactic, antiphlogistic, antihypertensive, spasmolytic, anti-rheumatic, and antithrombotic properties and are applicable in human and veterinary medicine to the treatment of asthma bronchiale and other allergic diseases, various inflammatory and rheumatic diseases, and thrombosis.
Processes for the preparation of ketoximes have been well known, as a matter of fact, and can be found in any manual on organic synthesis (cf. Weygand-Hilgetag, Organisch-Chemische Experimentierkunst). Several methods have been described in the literature for conversion of 1-aryl-alkane-1-ones with hydroxylamine-hydrochloride to oximes. Yet, in many instances conditions and rates of reaction, types of bases used, and other factors had not been optimally chosen in dependence on the parent ketone and its structure. The 1-(2-hydroxyphenyl)-alkane-1-on-oximes, within the framework of 1-aryl-alkane-1-on-oximes, are, typically, used as metal reagents in metal analysis and as selective metal extraction agents in liquid-liquid extraction (BRD-OS-2342878). 5-iso-nonyl-2-hydroxyacetophenone-oxime (SME 529 of Shell Chemicals) has assumed technical importance to the production of copper (Extr. Metal Copper Int. Symp. 1976, 1039). No information whatsoever has been recordable regarding a pharmaceutical application of these compounds in human or veterinary medicine.